Ethanolamine → tert-Butyl 4-{2-[3-(3-methoxypropyl)-1-methyl-1H-indol-5-ylmethyl]-3-methylbutyl}-2,2-dimethyloxazolidine-3-carboxylate

HRID 252399Notes

Reaction equation

HRID 252399 reaction equation
COCC(O[CH:7]([C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[N:32]([CH3:36])[CH:31]=[C:30]2[CH2:37][CH2:38][CH2:39][O:40][CH3:41])[CH:8]([CH:24]([CH3:26])[CH3:25])[CH2:9][CH:10]1[CH2:14][O:13][C:12]([CH3:16])([CH3:15])[N:11]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=O.C(CN)O>C(O)C.[Pd]>[CH3:41][O:40][CH2:39][CH2:38][CH2:37][C:30]1[C:29]2[C:33](=[CH:34][CH:35]=[C:27]([CH2:7][CH:8]([CH:24]([CH3:25])[CH3:26])[CH2:9][CH:10]3[CH2:14][O:13][C:12]([CH3:16])([CH3:15])[N:11]3[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:28]=2)[N:32]([CH3:36])[CH:31]=1

Participants

5

Reactant 2

HCID 700EthanolamineHCID 66887418tert-Butyl 4-(2-{(2-methoxyacetoxy)-[3-(3-methoxypropyl)-1-methyl-1H-indol-5-yl]methyl}-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 66888597tert-Butyl 4-{2-[3-(3-methoxypropyl)-1-methyl-1H-indol-5-ylmethyl]-3-methylbutyl}-2,2-dimethyloxazolidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2.80 g of tert-butyl 4-(2-{(2-methoxyacetoxy)-[3-(3-methoxypropyl)-1-methyl-1H-indol-5-yl]-methyl}-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate (diastereomer mixture) in 140 ml of ethanol is hydrogenated at 0° C. in the presence of 0.294 ml of ethanolamine and 3.34 g of 10% Pd/C over 3.5 hours. The reaction mixture is clarified by filtration and the filtrate is concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.48 (1:1 EtOAc-heptane). Rt=29.41 (gradient II).

Workup

  1. filtrationThe reaction mixture is clarified by filtration
  2. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-15272d6b22124a7a9b73c438cf1260db
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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